Synthesis and Crystal Structure of N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-ethylnitrous amide and N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-isopropylnitrous amide

Jinsen Chen; Pei Chen; Huaxin Yao; Jin Zhu

doi:10.14233/ajchem.2015.18383

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Issue Published : April 27, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Crystal Structure of N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-ethylnitrous amide and N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-isopropylnitrous amide

https://doi.org/10.14233/ajchem.2015.18383

Jinsen Chen

Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, Nanjing University, Nanjing 210093, P.R. China

Pei Chen

Huaxin Yao

Jin Zhu

Corresponding Author(s) : Jin Zhu

jinz@nju.edu.cn

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8
Article Published : April 27, 2015

Abstract

The title compound N-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-ethylnitrous amide (2, m.f. C₂₀H₃₂N₂O₅B₂) and N-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]phenyl)-N-isopropylnitrous amide (4, m.f. C₂₁H₃₄N₂O₅B₂) have been synthesized and characterized by elemental analysis, MS, IR, ¹H, ¹³C, ¹¹B NMR spectroscopies. In addition, their crystal structures were determined by single-crystal X-ray diffraction. The crystal of 2 belongs to monoclinic, space group P2₁/n with a = 6.3220(13), b = 28.910(6), c = 12.827(3) Å, b = 102.61(3)°, Z = 4, V = 2287.8(8) Å³, D_c = 1.167 g/cm³, μ(MoK_a) = 0.081 mm^-1, F(000) = 864, the final R = 0.0737 and wR = 0.1548 for 4209 observed reflections with I > 2s(I), while the compound 4 crystallizes in triclinic, space group P`1 with a = 6.8730(14), b = 10.827(2), c = 17.000(3) Å, a = 101.30(3), b = 92.07(3), g = 92.11(3)°, Z = 2, V = 1238.5(4) Å³, D_c = 1.116 g/cm³, μ(MoK_a) = 0.077 mm^-1, F(000) = 448, the final R = 0.0934 and wR = 0.1628 for 4546 observed reflections with I > 2s(I).

Keywords

Synthesis Crystal structure Nitroso group

Chen, J., Chen, P., Yao, H., & Zhu, J. (2015). Synthesis and Crystal Structure of N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-ethylnitrous amide and N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-isopropylnitrous amide. Asian Journal of Chemistry, 27(8), 2983–2986. https://doi.org/10.14233/ajchem.2015.18383

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References

N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995); doi:10.1021/cr00039a007.
I.A.I. Mkhalid, J.H. Barnard, T.B. Marder, J.M. Murphy and J.F. Hartwig, Chem. Rev., 110, 890 (2010); doi:10.1021/cr900206p.
J.F. Hartwig, Chem. Soc. Rev., 40, 1992 (2011); doi:10.1039/c0cs00156b.
J.F. Hartwig, Acc. Chem. Res., 45, 864 (2012); doi:10.1021/ar200206a.
J.-Y. Cho, M.K. Tse, D. Holmes, R.E. Maleczka Jr. and M.R. Smith III, Science, 295, 305 (2002); doi:10.1126/science.1067074.
G.A. Chotana, M.A. Rak and M.R. Smith III, J. Am. Chem. Soc., 127, 10539 (2005); doi:10.1021/ja0428309.
T. Ishiyama and N. Miyaura, Pure Appl. Chem., 78, 1369 (2006); doi:10.1351/pac200678071369.
B. Liu, Y. Fan, Y. Gao, C. Sun, C. Xu and J. Zhu, J. Am. Chem. Soc., 135, 468 (2013); doi:10.1021/ja3099245.
B. Liu, C. Song, C. Sun, S. Zhou and J. Zhu, J. Am. Chem. Soc., 135, 16625 (2013); doi:10.1021/ja408541c.
S. Kawamorita, T. Miyazaki, H. Ohmiya, T. Iwai and M. Sawamura, J. Am. Chem. Soc., 133, 19310 (2011); doi:10.1021/ja208364a.
When using 1 equiv. of B2pin2, para-Monosubstituted Product was Obtained in 40-50 % Besides the Disubstituted Products whose Structure was Confirmed by X-ray Diffraction Analysis (CCDC 1006981 for Substrate 3 and Monosubstitute Product of 1 is oil).
G.H. Sheldrick, SHELXS-97 and SHELXL-97. Program for Solution of Crystal Structures. University of Gottingen, Germany (1997).
F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. II, S1 (1987); doi:10.1039/p298700000s1.

References

N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995); doi:10.1021/cr00039a007.

I.A.I. Mkhalid, J.H. Barnard, T.B. Marder, J.M. Murphy and J.F. Hartwig, Chem. Rev., 110, 890 (2010); doi:10.1021/cr900206p.

J.F. Hartwig, Chem. Soc. Rev., 40, 1992 (2011); doi:10.1039/c0cs00156b.

J.F. Hartwig, Acc. Chem. Res., 45, 864 (2012); doi:10.1021/ar200206a.

J.-Y. Cho, M.K. Tse, D. Holmes, R.E. Maleczka Jr. and M.R. Smith III, Science, 295, 305 (2002); doi:10.1126/science.1067074.

G.A. Chotana, M.A. Rak and M.R. Smith III, J. Am. Chem. Soc., 127, 10539 (2005); doi:10.1021/ja0428309.

T. Ishiyama and N. Miyaura, Pure Appl. Chem., 78, 1369 (2006); doi:10.1351/pac200678071369.

B. Liu, Y. Fan, Y. Gao, C. Sun, C. Xu and J. Zhu, J. Am. Chem. Soc., 135, 468 (2013); doi:10.1021/ja3099245.

B. Liu, C. Song, C. Sun, S. Zhou and J. Zhu, J. Am. Chem. Soc., 135, 16625 (2013); doi:10.1021/ja408541c.

S. Kawamorita, T. Miyazaki, H. Ohmiya, T. Iwai and M. Sawamura, J. Am. Chem. Soc., 133, 19310 (2011); doi:10.1021/ja208364a.

When using 1 equiv. of B2pin2, para-Monosubstituted Product was Obtained in 40-50 % Besides the Disubstituted Products whose Structure was Confirmed by X-ray Diffraction Analysis (CCDC 1006981 for Substrate 3 and Monosubstitute Product of 1 is oil).

G.H. Sheldrick, SHELXS-97 and SHELXL-97. Program for Solution of Crystal Structures. University of Gottingen, Germany (1997).

F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. II, S1 (1987); doi:10.1039/p298700000s1.

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Synthesis and Crystal Structure of N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-ethylnitrous amide and N-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-isopropylnitrous amide

Corresponding Author(s) : Jin Zhu

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